Hypothesis: Droplet spreading on heterogeneous (chemical/structural) surfaces has revealed local disturbances that affect the advancing contact line. With droplet dewetting being less studied, we hypothesize that a receding droplet can be perturbed by localized heterogeneity which leads to irregular and discontinuous dewetting of the substrate. Experiments: The sessile drop method was used to study droplet dewetting at a wettability boundary. One-half of a hydrophilic surface was hydrophobically modified with either i) methyloctyldichlorosilane or ii) clustered macromolecules. A Lattice Boltzmann method (LBM) simulation was also developed to determine the effect of contact angle hysteresis and boundary conditions on the droplet dynamics. Findings: The two surface treatments were optimized to produce comparable water wetting characteristics. With a negative Gibbs free energy on the hydrophilic-half, the oil droplet receded to the hydrophobic-half. On the silanized surface, the droplet was pinned and the resultant droplet shape was a distorted spherical cap, having receded uniformly on the unmodified surface. Modifying the surface with clustered macromolecules, the droplet receded slightly to form a spherical cap. However, droplet recession was non-uniform and daughter droplets formed near the wettability boundary. The LBM simulation revealed that daughter droplets formed when θR > 164°, with the final droplet shape accurately described by imposing a diffuse wettability boundary condition.